A little under a decade ago, Arsenal had a bright young Italian striker in their youth ranks called Arturo Lupoli.
The Italian netted a prolific 27 goals in 32 games for Arsenal's reserves in his first season, going onto prosper alongside a certain Nicklas Bendtner.
However after a disappointing season long loan at Derby County where he scored just seven goals, doubts over his readiness to be a hit in the Premier League began to surface.
A craving to return to Italy also presented itself in the player's mind, who signed a pre-contract agreement with Fiorentina in 2007.
It would turn out to be a disastrous move.
Lupoli's was not given a chance, not selected for a single match, loaned out to Treviso, Norwich City and Sheffield United without success, as his career stalled.
Now 26 he plays for Serie B side Varese, utilised for just 67 minutes of football so far this season.
Speaking to Napoli Magazine ahead of Arsenal's Champions League tie, Lupoli has been lamenting his decision not to leave the Gunners - but his choice of destination.
He revealed he had a chance to move to Napoli, who were on the verge of a return to the top flight when he signed the pre-contract agreement with Fiorentina, but went for the guaranteed Serie A option in Fiorentina just in case, hinting it was not entirely his decision.
"I agreed to move to Naples, which was then in Serie B and was about to win the championship and go to Serie A.
"The management wanted me strongly, but unfortunately there were external pressures that led me to choose Fiorentina.
"That choice will always be my biggest regret. Going to Naples was my dream.
"Having the chance at 20-years-old, what's more the team I liked most in Italy, would have been amazing."
Was there more money for his agent in a move to Fiorentina? We can only speculate, but given his career trajectory since the decision it's easy to see why the former Gunner is kicking himself for not choosing the other path.
image: © ell-r-brown